Department of Chemistry, University of Basel, St. Johanns-Ring 19, Basel, CH-4056, Switzerland.
Department of Chemistry, University of Basel, Klingelbergstrasse 80, CH-4056 Basel, Switzerland.
Chem Soc Rev. 2016 May 3;45(9):2637-55. doi: 10.1039/c5cs00271k.
Developments in epigenomics, toxicology, and therapeutic nucleic acids all rely on a precise understanding of nucleic acid properties and chemical reactivity. In this review we discuss the properties and chemical reactivity of each nucleobase and attempt to provide some general principles for nucleic acid targeting or engineering. For adenine-thymine and guanine-cytosine base pairs, we review recent quantum chemical estimates of their Watson-Crick interaction energy, π-π stacking energies, as well as the nuclear quantum effects on tautomerism. Reactions that target nucleobases have been crucial in the development of new sequencing technologies and we believe further developments in nucleic acid chemistry will be required to deconstruct the enormously complex transcriptome.
表观基因组学、毒理学和治疗性核酸的发展都依赖于对核酸性质和化学反应性的精确理解。在这篇综述中,我们讨论了每个碱基的性质和化学反应性,并试图为核酸靶向或工程提供一些一般原则。对于腺嘌呤-胸腺嘧啶和鸟嘌呤-胞嘧啶碱基对,我们回顾了最近对其沃森-克里克相互作用能、π-π 堆积能以及核量子效应对互变异构的量子化学估算。靶向碱基的反应在新测序技术的发展中至关重要,我们相信需要进一步发展核酸化学来解构极其复杂的转录组。